Ethyl 2-(2-cyclohexenylthio)-4-thiazolecarboxylate



Patented at. 3, 1961 3,002,977 ETHYL 2-(2-CYCL0l-IEXENYLTHIO)-4-THIAZOLECARBOXYLATE John J. DAmico, Charleston, W. Va., assignor toMonsanto Chemical Company, St. Louis, Mo., a corporation of Delaware NoDrawing. Filed June 30, 1960, Ser. No. 39,782 1 Claim. (Cl. 260-302)This invention relates to ethyl 2-(2-cyclohexenylthio)-4-thiazolecarboxylate which may be prepared as follows: To a stirredsolution comprising 32 grams (0.169 mole) of ethyl2-mercapto-4-thiazolecarboxylate, 11.1 grams (0.169 mole) of 85%potassium hydroxide and 200 ml. of ethyl alcohol was added in oneportion 27.2 grams (0.169 mole) of 3-bromocyelohexene. A11 exothermicreaction set in causing the temperature to rise from 25 to 48 C. Afterstirring at 25-30 C. for 24 hours, 200 ml. of water and 300 ml. of etherwere added. The ether solution was separated, washed with water untilneutral to litmus and dried over sodium sulfate. The ether was removedin vacuo at a maximum temperature of 80-90 C. The product was obtainedin 61.5% yield as an amber oil. Analysis gave 4.8% nitrogen and 23.9%sulfur as compared to 5.2% nitrogen and 23.8% sulfur calculated fO'I'C12H15N02S2.

The product is an intermediate for synthesis of more complex moleculesand is an efiective miticide. Activity was demonstrated against thetwo-spotted spider mite, Tetmnychus telarius (L.). An aqueous emulsioncontaining 0.1% of ethyl 2-(2-eyclohexenylthio)-4-thiazoleoarboxylatewas employed for dipping thereinto infested leaves of plants. Contacteifects were observed on the infested leaves. On the dipped infestedplants 95% kill of all stages of the spider mite was obtained.

It is intended to cover all changes and modifications of the examples ofthe invention herein chosen for purposes of disclosure which do notconstitute departures from the spirit and scope of the invention.

What is claimed is:

Ethyl 2-(2-cyclohexenylthio) -4-thiazoleearboxy1ate.

No references cited.

